1-Phenylcyclohexanecarbonitrile → Cyclohexanemethylamine, 1-phenyl-

HRID 1270438Notes

Reaction equation

HRID 1270438 reaction equation
[C:1]1([C:7]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:1]1([C:7]2([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 751481-PhenylcyclohexanecarbonitrileHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 205110Cyclohexanemethylamine, 1-phenyl-

Procedure

A solution of 1-phenyl-cyclohexanecarbonitrile (11.0 g; 59 mmol) in tetrahydrifuran (100 mL) was cooled to 0° C. and treated with lithium aluminum hydride (11 g, 289 mmol) in several portions over the course of 0.5 h. When the addition of lithium aluminum hydride was complete the cooling bath was removed and the reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was cooled back to 0° C. and carefully quenched by dropwise addition of 2 N NaOH (approximately 20 mL), diluted with ethyl ether, filtered through a celite plug and dried (magnesium sulfate). C-(1-Phenyl-cyclohexyl)-methylamine was obtained as a colorless oil which was used without further purification. LCMS m/z=190.2 (M+H)+

Workup

  1. customwas removed
  2. temperatureThe reaction mixture was cooled back to 0° C.
  3. customcarefully quenched by dropwise addition of 2 N NaOH (approximately 20 mL)
  4. additiondiluted with ethyl ether
  5. filtrationfiltered through a celite plug
  6. dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record
ord-04ae1f56b9f14d6c9f22dcbc21b4f72c
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

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